


My Little Sammy

by DC_Derringer



Series: Winchester Affection [12]
Category: Supernatural
Genre: Anal, Anal Plug, Come play, Hair Kink, M/M, Multi, Pony Play, Whipping, face fucking
Language: English
Status: Completed
Published: 2012-12-17
Updated: 2012-12-17
Packaged: 2017-11-21 09:44:11
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,353
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/596284
Author URL: https://archiveofourown.org/users/DC_Derringer/pseuds/DC_Derringer
Summary: <blockquote class="userstuff">
              <p>Sam’s long hair inspires Castiel to dress Sam up like a pony and take him out for a ride.</p>
            </blockquote>





	My Little Sammy

When Dean got back to the motel room, Sam was kneeling on the floor, naked, with Castiel sitting on the bed beside him, brushing out his long hair with slow, careful strokes. This was actually pretty normal, as Castiel had recently become very fascinated by Sam’s hair, offering to brush it almost daily. Sam loved the attention and gave into Castiel’s whims every time.

The unusual part was that Sam was gagged with a horse bit, with a plug jutting out of his ass which sported a long, perky horse tail and, his hands were tied behind his back, wrists bound together with black straps of leather. Also, and this bit was particularly odd, there was some sort of colorful drawing of a heart with flowers springing out of it on Sam’s hip. On closer inspection, Dean saw that it was on the other hip as well.

“What is that?” Dean asked, pointing to the drawing on Sam’s hip.

“That is Sam’s cutie mark. In the cartoon, ‘My Little Ponies: Friendship is Magic,’ all the ponies bear one as an expression of their spirit and personality. I felt that Sam’s heart is like a garden of love.”

“Awww, my little Sammy!” Dean said, laughing through his words at Sam’s cutie mark. Sam huffed at him through his bit and gave him a glare as well. 

“There you are,” Castiel said, finally putting down the hair brush once Sam’s hair was a high sheen. Sam stood up and gave his hair a shake, much like a horse would, and gave an experimental whicker of approval. “Are you ready to go now?”

Sam nodded, and before Dean could ask where they were going, they were already there, blinked into an open meadow secluded from anyone who might notice a giant naked man dressed up like a pony. But it wasn’t just any meadow; Castiel had spent some time preparing for his game with Sam. The meadow had a lightly beaten dirt path that twisted around leading it over fences, trenches, and even a small muddy pond.

Sam whickered again, and stamped his feet eagerly at the sight of the track he would be expected to run, and Castiel smiled when he saw that Sam was pleased with his work.

“Wow, you put a lot of thought into this,” Dean said after giving a low whistle to show his approval of the track. “So you’re going to make Sammy run this track with his dick slapping all over the place?”

“Yes, and I want you to encourage him, so he will run his very best,” Castiel said with a sly smile as he handed Dean a riding crop. “I’ve often wondered which of you could run faster.”

Sam frowned around his bit at the sight of the riding crop, and as a wicked smile turned up Dean’s lips, Sam suddenly took off running down the dirt path. Dean was surprised for only a second by Sam’s unexpected start, and then took off running after his brother, laughing gleefully and brandishing the crop over his head.

Because of his long legs and the fact that Dean ate cheeseburgers almost every day Sam usually had Dean beat in a flat out run. But the big plug shoved up his ass wasn’t very comfortable when he was trying to run and leap over fences. Also, with his arms tied behind his back, he lost some of his balance, and had to run more carefully. That said, his usual easy lead against Dean slimmed down, and after clearing the first fence, he felt the first bite of the crop on his ass.

“C’mon Sammy, you can run faster than that!” Dean cheered, brandishing the crop again to clip Sam’s thighs. Sam let out a yelp and took a sharp turn to stay on the path and then leaped a deep trench. However, Dean just ran around the obstacles.

Sam kept his lead up as best he could, but Dean kept nipping at his heels and catching him with the crop when he least expected it. Chest pounding, and heart racing, the sting of the leather on his naked flesh made him feel even hotter and he tried to do his best on the obstacle course. 

Finally, there was the last obstacle, a shallow muddy pond that Sam had to clear in one bound after a long, straightaway run. There’d be no chance for him to zig and zag, so Dean would be right on his heels, whipping him the whole way. He kind of hoped Dean ended up in the mud while Castiel praised him for a good run. Maybe he would brush his hair again.

As Sam got up on the last run, he put all his last energy into it, getting up as much speed as he could so he could clear the pond. Dean whipped him a few times, but it only spurred him on faster, and with only a few feet to go, he felt Dean fall back to avoid the pond. Good. Sam knew he could make it. He pounded up those last few feet, his long legs making the ground fly underneath him, and then right on the rim of the water, he leapt, launching into the air. He caught his reflection in the pool underneath him, for just a second, and then the other side was coming up, just another second. He was going to make it.

And then his foot caught on the other end of the pond, just shy of dry land, and he slipped, slid, and fell splashing into those few, cold, squishy inches of mud. Sam rolled over so he wouldn’t drown, and with his arms still behind his back, struggled up onto his knees, and then to his feet. 

On the other side of the pond, Dean had doubled over laughing and pointing at Sam, who was surely a disgusting, muddy mess. Sam huffed and stomped his feet in the mud, annoyed that he hadn’t cleared the pond. Even Castiel was smiling a little bit as he watched Sam climb out of the pond, but he was at least kind enough to look bad about it.

“You ran very well, Sam,” Castiel said, looking up at Sam proudly. Sam perked up at this a little bit. “But I think you need a bath and another thorough brushing. Would you like that?”

Sam nodded his head and stomped his foot to show that he liked that idea. Castiel smiled, and with Dean still wiping tears from his eyes, they walked over to a small stream not far from the obstacle course. Sam stepped in gingerly, since the water was cold, but as soon as Dean got close to the edge, he barreled in, splashing water everywhere. Soon, Dean stripped his clothes off as well, and jumped into the stream with Sam. Castiel took his cue, and soon joined them.

“You know Cas,” Dean said, while Castiel was working mud out of Sam’s hair by gently tilting him back in the water. “Having your pony run an obstacle course is just one of many ways to give him some much needed exercise.”

“Did you have something else in mind?” Castiel asked.

“He’s a pony Cas. You’re supposed to ride him,” Dean said with a smirk. Sam smirked as well, as best he could around his bit, and gave a whinny of approval at Dean’s suggestion.

“I don’t think that would be very comfortable for Sam,” Castiel said doubtfully. “Aren’t I rather heavy for a human?”

“Don’t worry. I know a position so Sam will be perfectly comfortable.”

Leering at each other, Sam and Dean climbed out of the stream and walked over to a smooth, grassy bank. Dean released Sam’s arms from behind his back and urged his brother to lie down. They then both beckoned Castiel over.

“You should be very comfortable riding your pony in this position,” Dean said, guiding Castiel so that he stood over Sam, straddling his hips. Castiel considered this for a moment, looking between Sam and Dean with some confusion, until his face lit up with understanding.

“Ohhh, riding is like breeding. It is a euphemism for sex,” Castiel said proudly.

Both brothers rolled their eyes affectionately, and Dean urged Castiel down on his knees, straddling Sam’s cock, which was rising up with interest at the prospect of Castiel riding him. A bottle of lube appeared in Castiel’s hand and he offered it to Dean, who took it and eagerly spread some lube on his fingers so that he could get Castiel loose and ready. 

While Dean worked his fingers into Castiel’s hole, Castiel set about brushing Sam’s wet hair again, fluffing it out and drying it, while Sam murmured his pleasure and shook his head with approval. Getting groomed while Castiel was prepped for sex more than made up for the tumble in the muddy water.

“I think Cas has a hair fetish,” Dean said. “Do you want to braid Sam’s hair now?”

“Perhaps later. I am ready for my ride now,” Castiel said. Dean withdrew his fingers and allowed Castiel to lower himself over the head of Sam’s cock. But he paused for a moment and looked at Sam’s face. “Dean, perhaps you should take out Sam’s bit. I don’t want his mouth to be sore. Just make sure he isn’t able to speak. He’s still my little pony,” Castiel added with a smirk.

Dean smirked back, getting the idea, and unstrapped the bit from Sam’s mouth. Sam worked his jaw for a few seconds, stretching and clenching his teeth, and then licking his lips. Eventually, he sat propped up on his elbows and opened his mouth for Dean. He also got Castiel’s idea.

At the same time Castiel slid down onto Sam’s cock, Dean slid into Sam’s mouth. All three of them let out soft, satisfied sounds as they connected. Dean slowly threaded his hands into Sam’s hair, appreciating the length which gave him a good grip, and started leading Sam’s head, tugging him back and forth on his cock. Sam looked up at him, smirking as Dean used his hair like reigns. 

“I take back everything bad I ever said about Sam’s long hair,” Dean said, thrusting harder into Sam’s slack mouth. “I love this stuff.”

“It is useful,” Castiel said, while he thrust himself up and down on Sam’s cock. Sam bucked up occasionally, jerking Castiel harder, and dredging a sharp cry from Castiel’s throat. But Castiel took it in stride, and eventually started riding faster and harder, bouncing on Sam’s cock like it was a hard gallop, racing to find him pleasure. 

“C’mon, stud,” Dean husked, working into Sam’s mouth, but glancing over his shoulder as Castiel bounced away. “Suck that dick. Wanna come straight down your throat.”

Sam moaned around Dean’s cock, wanting to taste his brother’s come. He sucked harder, and let Dean lead him, forcing his head back and forth almost roughly. The tug on his hair was almost painful, but he liked it, the ache making the pleasure burn all that much hotter, until finally, there was an extra hard pull, and Castiel clenched around him, and he’d already been petted and stroked and run around all day, so he went off. His hips jerked up hard inside Castiel, giving him a real ride, and then he was spilling, moaning his orgasm around Dean’s cock while he pulsed thickly into Castiel’s body.

Castiel let out a small, surprised murmur, delighting in the feel of Sam going off inside him. He squirmed at each pulse, grinding against Sam’s still hard cock and stroking himself in time. A few more hard jerks, and he went off too, spilling his come all over Sam’s belly.

Dean’s hands had gentled as Sam hit his orgasm, but the sight of that sexy, sleepy look on Sam’s face just after coming always did Dean in. He was ready, and he jerked Sam’s hair again, making his brother’s eyes snap open. Dean started thrusting hard again, and faster, and Sam relaxed as best he could to take the cock deep into his throat. Every other thrust or so dipped into the back of his throat, and his eyes watered a little, trying not to choke on Dean’s dick.

“Almost there, Sammy,” Dean grunted as Sam looked up at him hungrily. Sam moaned some more and closed his eyes. Dean smiled and pumped faster, getting himself right to the edge, and then, just as he was about to spill, he pulled out. The first spurt of come hit Sam in the face, and then the rest was carefully angled into Sam’s hair, Dean holding it tightly so that Sam couldn’t turn away.

“Dean!” Sam yelled as Dean spilled his load into his hair, and he couldn’t get away without getting his scalp ripped out. Dean chuckled a little and wiped the tip of his dick onto Sam’s crown before he finally pulled away.

“It’s good for your hair,” Dean insisted.

“You are so-Mmmf!” Sam started to yell, about to get up and dislodge Castiel to chase after his brother, when suddenly, the horse bit was back in his mouth again and strapped in tightly around his head. Sam whipped around to glare at Castiel.

“Ponies are not allowed to speak,” Castiel said in a reprimanding tone.

“Mmmmf!” Sam shouted through the bit, pointing at the mess Dean had left in his hair. Castiel looked at it for a moment, and then reached forward to smooth the semen further into Sam’s hair, spreading it around.

“It’ll make your mane nice and shiny,” Castiel insisted, much like Dean had before. Sam growled, but there was no anger in it, just his usual affection, though it was reluctant.

By the end of the afternoon, Dean and Castiel had each had two more rides each on their pony, and added a little more hair product to Sam’s hair, refusing teasingly and affectionately from rinsing it out. It wasn’t until the sun set that they finally let Sam be a man again and rinse out his hair.


End file.
